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The J in J.Crew

On the day I first met her, Lyons wore a loud combination of neon-pink T-shirt, color-blocked Céline skirt, and a dozen mismatched bangles. In navy Manolo Blahnik heels, she was taller than Dwyane Wade. It worked, somehow, just as her feathered skirts, gold sequined pants, and Henry Kissinger glasses somehow work. Where feathers and sequins meet J.Crew is largely a matter of styling, and though Lyons dislikes the word preppy, her choices always invoke the core prep values of ease, cleanliness, and conservatism. If her company has always prized a kind of sartorial comfort—nothing too tight, too short, too synthetic—then Lyons, with her bare face and occasional bralessness, is what happens when comfort meets chic.

The same goes for her Park Slope townhouse, which is a merry (but careful) assemblage of fur throws, drooping roses, and worn staircases. Her environs, as well as Lyons’s husband and son, have been heavily photographed—or, less charitably, branded—by J.Crew since 2008, when the company introduced the “Jenna’s Picks” feature in its catalogue and on its website. Jenna’s Picks, which collects her favorite items from J.Crew and beyond, now comes out fourteen times a year to the ardent scrutiny of blogs like I Love J.Crew and J.CrewAholics, and points of contact between Lyons and J.Crew customers have quickly multiplied. She has given Oprah a tour of her closet, shared style tips with Lucky, Glamour, Details, and InStyle, and appeared on the cover of the late Domino magazine. (“Every girl I know has saved that issue,” says Anthony Sperduti, a co-founder of the store-cum-advertising agency Partners & Spade and a friend of Lyons’s.) At this point, she has shared with customers her favorite ice-cream sandwich, lip color, bangle, spectator pump, notebook, bikini, statement necklace, diaper bag, and distressed sneaker. “I can’t tell you the amount of women for whom Jenna invariably comes up in conversation,” Sperduti says. “I don’t know that many designers in her role that you could say the same thing about. Not from a company of that scale.”

An unexpected measure of Lyons’s celebrity was taken this April when a catalogue photo of Lyons and her son, Beckett, ignited a scandal nicknamed Toemaggedon by Jon Stewart. The project began innocently enough, when J.Crew’s catalogue director asked Lyons if she would document her weekend with a few snapshots for a “Saturday With Jenna” weekendwear promotion. Lyons recruited her husband, the artist Vincent Mazeau, to take some photos: a toasted English muffin, comfy moccasins, the New York Times, and Lyons painting Beckett’s toenails neon pink. The toenail image, with all the liberal gender-bending it implied, immediately popped up on the network news shows, and Fox News’ website featured an anti-Lyons piece advancing vaguely eugenicist notions. (“Why not make race the next frontier?” wrote Keith Ablow, a psychiatrist and Fox News contributor, referring to the identity crisis Lyons had apparently exposed her son to. “What would be so wrong with people deciding to tattoo themselves dark brown and claim African-American heritage?”) On The Daily Show, Stewart upbraided the newscasters for treating the photograph as though it were “a story about incest or cannibalism.”

Lyons found out about the clamor through a J.Crew Google alert. Neither she nor the company chose to comment. “It was about sweatpants and moccasins and reading the paper,” she says. “And that’s what we were doing: I was painting my nails and Beckett wanted his nails painted, too. I’m not surprised that he was interested in what I was doing. My God, my toes went from white to hot pink—it was very exciting.”

Not a political statement, maybe, but Lyons’s inclusion of her child in the catalogue, along with her slippers and breakfast, is precisely the kind of statement that makes her appealing to an audience looking for personalized, customizable fashion. “You can be running one of the biggest fashion retailers in America, but at the same time, you want it to feel tangible and touchable,” says Mark Holgate, fashion-news director at Vogue. “You want people to connect with it.” Her style, he says, is “nuanced, personal, layered, a little vintage. With the rise of the eBay generation, people are interested in making a statement with things that feel personal rather than just new.” Lyons, he says, “understands how to bring together the fashion impulse with the sense of lifestyle.”

This is not a role that Lyons will readily admit to, and when I bring up a word that is often applied to her, she expresses a shuddering distaste. “My goal is not to be a tastemaker,” she says. “It has never been that. I don’t consider myself that at all. The idea that you can make taste or influence someone’s taste is a very precarious and overly presumptuous concept.” But isn’t that, in large part, what she is paid to do? Lyons frowns. “Hubris is not so cute.”